Prevent Email Horror with a 2-Minute Send Delay

Marketing manager Grier was just plain tired of colleagues playing the expert in her domain. When a designer sent her an e-mail questioning her choice of quotes for a new product brochure, she snapped.

“How about you do your job, and I’ll do mine!” she typed back rapidly and punched “send.” A split second later, she wished she hadn’t. Her better self knew that a dose of circumspection would have saved her from the now face-to-face damage control she had to do with an offended colleague.

When was the last time you sent an email that seconds later you wished you hadn’t? Maybe you forgot an attachment? Maybe you forgot to check spelling or to delete the e-trail below your message that had personal comments — too personal. Or just maybe, like the fictitious (but realistic) person I’m calling Grier, you were irritated, and you realized you should have slept on your response before firing it off?

You and Your Team

It’s for these sorts of reasons that several years ago I decided to put a two-minute delay on all of my office emails. It’s come to my rescue many a time, allowing me to pop into my outbox and fix inaccuracies; add the PowerPoint file I forgot to attach; or re-edit a sensitive message for nuance. I’d love to say it’s simple to get started, but if you use the version of Outlook that I use — Outlook 2013 — you’ll need to navigate a rabbit’s warren of clicks and commands. It’s worth it.

Go to the “Home” tab and click on the “Rules” drop down

Choose “Manage Rules and Alerts”

Under “Email Rules” choose “New Rule” and under “Start from a blank rule” click on “Apply rule on messages I send.” Click “Next,” which will show conditions — you don’t need to choose any of these, just click “Next” again.

On the final menu (the “Actions” page), check “Defer delivery by _ minutes” and fill in the blank. I choose two minutes, because it often takes me a minute to realize what I’ve forgotten!

Click “Next,” and fill in any exceptions to your new rule. Then, click “Next,” and “Finish” (Don’t forget this last step, or all your clicks will be for naught.)

If you use Gmail, you’re in luck, as Google just added an “undo send” feature, which is much simpler. To enable it:

Go to the little cog icon in the upper right-hand corner and select “Settings.”

Look a third of the way down the page for the “Undo Send” section.

Check “Enable Undo Send” and then choose between 5, 10, 20 and 30 second windows of unsendability. Again, I’d go for longest interval to give your mental red flags a chance to flutter.

Make sure you hit “Save Changes” at the bottom.

Three Common Saves

Preventing a pickle like Grier’s is one way that a delayed send can save you from yourself. But it’s likely not the most common. In my experience, the top three rescues are from crossed messages, forgotten credits, and ingratitude.

Crossed messages occur when one reads e-mails out of order, answering a question that a subsequent email has rendered obsolete. Or, when one efficiently answers screens full of email offline during a flight — only to synch up hours later and find the criteria changed when you were somewhere over Nebraska. Then there’s the group e-mail, where replies cross in the ether, one carrying info that affects the other.

Exclusion can happen, unwittingly, in messages acknowledging broad-based teams. Darn it if one doesn’t realize, seconds after clicking send, that she forgot to acknowledge the social media associate, or the company founder!

My favorite save is from sounding ungrateful. No matter how much we appreciate the shoulders we stand on, too often our emails cut directly to the task at hand. Just as they sail away, we realize that we meant to open with thanks, and close with appreciation. Mercifully, a two-minute delay gives us a second chance to do just that.

The Downside

No change lacks drawbacks, and there are at least two when it comes to delayed sends. For one, in a meeting or on a conference call, you can’t circulate a document right away away. In our age of instant gratification, people can get frustrated waiting for your email to clear your inbox (even if it’s just two minutes!). For another, when responding to email on planes right up until the flight attendant calls for shutting down electronics, you have to find ways to sneak an extra few minutes of power.

But these grievances pale in comparison to the upside. In a digital world, we still need to think before we speak, but with a delayed send, we can rethink after we email.